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| United States Patent |
5,066,641
|
|
Narula
, et al.
|
November 19, 1991
|
3,5,5-trimethylhexanal oxime and organoleptic uses thereof
Abstract
Described is 3,5,5-trimethylhexanal oxime defined according to the
structure:
##STR1##
and organoleptic uses thereof in augmenting or enhancing the aroma of
perfume compositions, colognes and perfumed articles including but not
limited to solid or liquid anionic, cathionic, nonionic and zwitterionic
detergents, perfume polymers, fabric softener compositions, fabic softener
articles, cosmetic powders and hair preparations.
| Inventors:
|
Narula; Anubhav P. S. (Hazlet, NJ);
De Virgilio; John J. (Freehold, NJ);
Van Elst; Jan T. (Et Hilversum, NL)
|
| Assignee:
|
International Flavors & Fragrances Inc. (New York, NY)
|
| Appl. No.:
|
588844 |
| Filed:
|
September 27, 1990 |
| Current U.S. Class: |
512/25; 510/101; 564/268 |
| Intern'l Class: |
A61K 007/46 |
| Field of Search: |
512/25,27
564/268
|
References Cited
U.S. Patent Documents
| 3637533 | Jan., 1972 | Dahill | 252/522.
|
| 3745213 | Jul., 1973 | Nysted | 512/4.
|
| 4017634 | Apr., 1977 | Lam et al. | 424/300.
|
| 4544714 | Oct., 1985 | Ochsner | 252/522.
|
| 4758548 | Jul., 1988 | Granlick et al. | 512/25.
|
| 4863631 | Sep., 1989 | Sprecker et al. | 252/174.
|
| Foreign Patent Documents |
| 2723636 | Dec., 1978 | DE | 512/27.
|
Primary Examiner: Reamer; James H.
Attorney, Agent or Firm: Liberman; Arthur L.
Claims
What is claimed is:
1. The 3,5,5-trimethylhexanal oxime having the structure:
##STR22##
2. A process for augmenting or enhancing the aroma of a perfume
composition, cologne or perfumed article comprising the step of adding to
said perfume composition, cologne or perfumed article an aroma augmenting
or enhancing quantity of the product defined according to claim 1.
3. A perfume composition comprising a perfume base and an aroma augmenting
or enhancing quantity of the compound of claim 1.
4. A perfumed article comprising a perfumed article base and intimately
admixed therewith an aroma augmenting or enhancing quantity of the
compound defined according to claim 1.
5. A perfumed polymer comprising a polymeric base and intimately admixed
therewith an aroma augmenting or enhancing quantity of the compound
defined according to claim 1.
Description
BACKGROUND OF THE INVENTION
The present invention relates to the compound 3,5,5-trimethylhexanal oxime
and uses thereof to alter, modify or enhance the aroma of consumable
materials.
There has been considerable work performed relating to substances which can
be used to impart (modify, augment or enhance) fragrances too (or in)
various consumable materials. These substances are used to diminish the
use of natural materials, some of which may be in short supply and to
provide more uniform properties in the finished product.
Long-lasting and substantive green, vetivert, woody, earthy, orris, minty,
camphoraceous, cassis and grapefruit aromas with minty, camphoraceous,
green, herbaceous, vetivert and galbanum topnotes are highly desirable in
several types of perfume compositions, perfumed articles and colognes.
The use of oximes is well known in perfumery. Furthermore, the use of
oximes is known for their value as intermediates in preparing other
compounds such as nitriles.
U.S. Pat. No. 4,863,631 issued on Sept. 5, 1989 (Sprecker, et al) discloses
the genus of compounds having the structure:
##STR2##
wherein N is 0 or 1 as an intermediate in producing nitriles, which
nitriles are useful as perfumery ingredients.
However, U.S. Pat. No. 3,637,533 issued on Jan. 25, 1972 (Dahill) discloses
the use of 3,7-dimethyloctanal oxime having the structure:
##STR3##
for use in perfumery at Example VI, column 5 and Example XXIII, column 12.
Furthermore, the Dahill reference claims a perfume-containing composition
comprising an olfactory effective amount of an oxime of a branched chain
ethylenic unsaturated hydrocarbyl aldehyde . . . having from 7-10 carbon
atoms.
U.S. Pat. No. 4,017,634 issued on Apr. 12, 1977 (Lam, et al.) discloses as
a chemical intermediate the compound having the structure:
##STR4##
Nothing of the prior art, however, discloses the 3,5,5-trimethylhexanal
oxime having unexpected, unobvious, and advantageous organoleptic
properties.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is the GLC profile for the reaction product of Example I containing
the compound having the structure:
##STR5##
(Conditions: SE-30 column programmed at 220.degree. C. isothermal).
FIG. 2 is the NMR spectrum for the compound having the structure:
##STR6##
produced according to Example I.
FIG. 3 is the infra-red spectrum for the compound having the structure:
##STR7##
produced according to Example I.
FIG. 4 represents a cutaway side elevation view of apparatus used in
forming perfume polymers which contain embedded therein the
3,5,5-trimethylhexanal oxime of our invention.
FIG. 5 is a front view of the apparatus of FIG. IV looking in the direction
of the arrows.
DETAILED DESCRIPTION OF THE DRAWINGS
Referring to FIGS. IV and V, there is provided a process for forming
scented polymer elements (wherein the polymer may be a thermoplastic
polymer such as low density polyethylene or polypropylene or copolymers of
ethylene and vinyl acetate or mixtures of polymers and copolymers such as
copolymers of ethylene and vinyl acentat and polyethylene) such as pellets
useful in the formation of plastic particles useful in fabricating certain
articles which may be perfumed. This process comprises heating the polymer
or mixture of polymers to the melting point of said polymer or mixture of
polymers, e.g., 250.degree. C. in the case of low density polyethylene.
The lower most portion of the container is maintained at a slightly lower
temperature and the material in the container is taken off at such
location for delivery through the conduit. Thus, referring to FIGS. IV and
V, in particular, the apparatus used in producing such elements comprises
a device for forming the polymer containing the perfume, e.g. polyethylene
or polyethylene-polyvinyl acetate or mixtures thereof or polypropylene,
which comprises a vat or container 212 into which the polymer taken alone
or in admixture with other copolymers and the perfuming substance which is
at least the 3,5,5-trimethylhexanal oxime of our invention and other
compatible perfumes is placed. The container is closed by means of an
air-tight lid 228 and clamped to the container by bolts 265. A stirrer 273
traverses the lid or cover 228 in an air-tight manner and is rotatable in
a suitable manner. A surrounding cylinder 212A having heating coils which
are supplied with electric current through cable 214 from a rheostate or
control 216 is operated to maintain the temperature inside the container
212 such that the polymer in the container will be maintained in the
molten or liquid state. It has been found advantageous to employe polymers
at such a temperature that the viscosity will be in the range of 90-100
sayboldt seconds. The heater 218 is operated to maintain the upper portion
of the container 212 within a temperature range of, for example,
220.degree.-270.degree. C. in the case of low density polyethylene. The
bottom portion of the container 212 is heated by means of heating coils
212A regulated through the control 220 connected thereto through a
connecting wire 222 to maintain the lower portion of the container 212
within a temperature range of 220.degree.-270.degree. C.
Thus, the polymer or mixture of polymers added to the container 212 is
heated from 10-12 hours, whereafter the perfume compostion or perfume
material which contains at least the 3,5,5-trimethylhexanal oxime of our
invention is quickly added to the melt. Generally, about 10-45 percent by
weight of the resulting mixture of the perfumery substance is added to the
polymer.
After the perfume material is added to the container 212, the mixture is
stirred for a few minutes, for example, 5-15 minutes and maintained within
the temperature ranges indicated previously by the heating coil 212A. The
controls 216 and 220 are connected through cables 224 and 226 to a
suitable supply of electric current for supplying the power for heating
purposes.
Thereafter, the valve "V" is opened permitting the mass to flow outwardly
through conduit 232 having a multiplicity of orifices 234 adjacent to the
lower side thereof. The outer end of the conduit 232 is closed so that the
liquid polymer in intimate admixture with at least the
3,5,5-trimethylhexanal oxime of our invention or mixture of
3,5,5-trimethylhexanal oxime with other perfumery materials (optionally),
will continuously drop or drip through the orifices 234 downwardly from
the conduit 232. During this time, the temperature of the polymer
intimately admixed with the perfumery substance in the container 212 is
accurately controlled so that a temperature in the range of from about
240.degree. C.-250.degree. C. for example, (in the case of low density
polyethylene) will exist in the conduit 232. The regulation of the
temperature through the controls 216 and 220 is essential in order to
insure temperature balance to provide for the continuous dripping or
dropping of molten polymer intimately admixed with the perfume substance
which is all of or which contains the 3,5,5-trimethylhexanal oxime of our
invention through the orifices 234 at a rate which will insure the
formation of droplets 236 which will fall downwardly onto a moving
conveyor belt 238 caused to run between conveyor wheels 240 and 242
beneath the conduit 232.
When the droplets 236 fall onto the conveyor 238, they form pellets 244
which harden almost instantaneously and fall off the end of conveyor 238
into a container 250 which is advantageously filled with water or some
other suitable cooling liquid in order to insure the rapid cooling of each
of the pellets 244. The pellets 244 are then collected from the container
250 and utilized for the formation of functional products, e.g., garbage
bags and the like.
THE INVENTION
The invention provides 3,5,5-trime hylhexanal oxime having the structure:
##STR8##
The 3,5,5,-trimethylhexanal oxime of our invention produced according to
the process of our invention is capable of augmenting or enhancing green,
vetivert, woody, earthy, orris, minty, camphoraceous, cassis and
grapefruit aromas with minty, camphoraceous, green, herbaceous, vetivert
and galbanum topnotes in perfume compositions, colognes and perfumed
articles including soaps, anionic, cationic, nonionic and zwitterionic
detergents, fabric softener articles and perfumed articles.
In carrying out the process for preparing the 3,5,5-trimethylhexanal oxime
of our invention, the aldehyde having the structure:
##STR9##
is reacted with a hydroxyl amine salt having the structure: wherein Y
represents an anion such as sulfate, chloride or bromide and P is 1 or 2
followed by reaction with base to form the oxime which is the
3,5,5-trimethylhexanal oxime of our invention, having the structure.
##STR10##
In carrying out the reaction of the compound having the structure:
##STR11##
with the compound having the structure:
##STR12##
this reaction is carried out at 0.degree.-40.degree. C. at atmospheric
pressure. The reaction is a two stage reaction with the first stage being
the reaction of the aldehyde having the structure: with a hydroxyl amine
salt having the structure:
##STR13##
(e.g. hydroxylamine hydrochloride or hydroxylamine sulfate). The second
stage of the reaction is reaction with base with or without inert solvent.
The base can be sodium hydroxide or calcium hydroxide.
The 3,5,5-trimethylhexanal oxime of our invention and one or more auxiliary
perfume ingredients, including, for example, hydrocarbons, alcohols,
ketones, aldeydes, nitriles, esters, lactones, ethers, synthetic essential
oils and natural essential oils may be admixed so that the combined odors
of the individual components produce a pleasant and desired fragrance,
particularly and preferably in the green and woody fragrances.
Such perfume compositions usually contain (a) the main note or "bouquet" or
foundation stone of the composition; (b) modifiers which round off and
accompany the main note; (c) fixatives which include odorous substances
which lend a particular note to the perfume throughout all stages of
evaporation and substances which retard evaporation; and (d) topnotes
which are usually low boiling fresh smelling materials.
In perfume compositions, it is the individual components which contribute
to their particular olfactory characteristics, however, the overall
sensory effect of the perfume composition will be at least the sum total
of the effects of each of the ingredients. Thus, the
3,5,5-trimethylhexanal oxime of our invention can be used to alter, modify
or enhance the aroma characteristics of a perfume composition, for
example, by utilizing or moderating the olfactory reaction contributed by
another ingredient in the composition.
The amount of the 3,5,5-trimethylhexanal oxime which will be effective in
perfume compositions as well as in perfumed articles and colognes depends
upon many factors, including the other ingredients, their amounts and the
effects which are desired. It has been found that perfume compositions
containing as little as 0.05% of the 3,5,5-trimethylhexanal oxime of our
invention or even less (e.g., 0.02%) can be used to impart green,
vetivert, woody, earthy, orris, minty, camphoraceous, cassis and
grapefruit aroma nuances with minty, camphoraceous, green, herbaceous,
vetivert and galbanum topnotes to soaps, cosmetics, detergents (including
anionic, cationic, nonionic and zwitterionic solid or liquid detergents).
The amount employed can range up to 70% of the fragrance components and
will depend upon considerations of cost, nature of the end product, the
effect desired on the finished product and the particular fragrance
sought.
The 3,5,5-trimethylhexanal oxime of our invention is useful (taken alone or
together with other ingredients in perfume compositions) in detergents and
soaps, space odorants and deodorants, perfumes, colognes, toilet waters,
bath preparations such as lacquers, brilliantines, pomades and shampoos;
cosmetic preparations, such as creams, deodorants, hand lotions and sun
screens; powders such as talcs, dusting powders, face powders and the
like. As little as 0.25% of the 3,5,5-trimethylhexanal oxime of our
invention will suffice to impart an intense and substantive green,
vetivert, woody, earthy, orris, minty, camphoraceous, cassis and
grapefruit aroma profile with minty, camphoraceous, green, herbaceous,
vetivert and galbanum topnotes to floral and woody perfume formulations.
Generally, no more than 5% of the 3,5,5-trimethylhexanal oxime of our
invention based on the ultimate end product is required to be used "as-is"
or in the perfume composition.
Furthermore, as little as 0.25% of the 3,5,5-trimethylhexanal oxime of our
invention will suffice to impart such aroma to perfumed articles per se,
whether in the presence of other perfume materials or whether used by
itself. Thus, the range of use of the 3,5,5-trimethylhexanal oxime of our
invention in perfumed articles may vary from about 0.25% up to about 5% by
weight based on the total weight of the perfumed article.
In addition, the perfume composition or fragrance composition of our
invention can contain a vehicle, or carrier for the 3,5,5-trimethylhexanal
oxime of our invention. The vehicle can be a liquid such as a non-toxic
alcohol, e.g. ethanol, a non-toxic glycol, e.g. propylene glycol or the
like. The carrier can also be an absorbent solid, such as a gum (e.g., gum
arabic), or components for encapsulating the composition by mean of
coacervation (such as gelatin).
It will thus be apparent that the 3,5,5-trimethylhexanal oxime of our
invention can be utilized to alter, modify or enhance aroma of perfume
compositions, colognes and perfumed articles.
The following Example I serves to illustrate a process for producing the
3,5,5-trimethylhexanal oxime of our invention. Examples following Example
I in general serve to illustrate organoleptic utilities of the
3,5,5-trimethylhexanal oxime of our invention. All parts and percentages
given herewith are by weight unless otherwise specified.
EXAMPLE I
PREPARATION OF 3,5,5-TRIMETHYLHEXANAL OXIME
##STR14##
Into a 3 liter reaction flask equipped with stirrer, thermometer, reflux
condenser, heating mantle and cooling bath is placed 415 grams (2.5 moles)
of hydroxyl amine sulfate and 1600 ml water. The resulting mixture is
stirred until homogeneous.
The temperature of the resulting mixture is cooled to 10.degree. C. Rapidly
over a period of 5 minutes, 500 grams (3.5 moles) of the compound having
the structure:
##STR15##
is added to the reaction mass.
Over a period of 1 hour while maintaining the reaction temperature at
55.degree.-57.degree. C., 460 grams (5.75 moles) of sodium hydroxide are
added to the reaction mass.
The reaction mass now exists in two phases; an organic phase and an
inorganic phase. The organic phase is separated from the inorganic phase.
The organic phase is washed with four 1800 ml portions of saturated sodium
chloride solution.
The resulting product is then rushed over to yield 473 grams of product
(86% yield). The resulting product is then fractionally distilled on
1".times.12" Goodloe column yielding the following fractions:
______________________________________
Vapor Liquid
Fraction Temp. Temp. Vaccum Weighted
No. (.degree.C.)
(.degree.C.)
mm/Hg Fraction
______________________________________
1 80 91/ 2.03 25
2 93 98 5.80 15
3 93 99 5.76 23
4 93 98 5.73 32
5 93 98 5.73 35
6 93 98 5.73 39
7 97 101 5.65 40
8 93 100 5.70 37
9 93 99 5.65 44
10 94 100 5.65 35
11 94 101 5.60 35
12 94 102 5.60 28
13 94 117 5.54 13
14 94 180 5.58 6
15 94 210 5.76 2
______________________________________
FIG. 1 is the GLC profile of the reaction product containing the compound
having the structure:
##STR16##
FIG. 2 is the NMR spectrum for the compound having the structure:
##STR17##
FIG. 3 is the infra-red spectrum of the compound having the structure:
##STR18##
The resulting compound has a green, vetivert, woody, earthy, orris, minty,
camphoraceous, cassis and grapefruit aroma profile with minty,
camphoraceous, green, herbaceous, vetivert and galbanum topnotes.
EXAMPLE II
The following Chypre formulation is prepared:
______________________________________
Ingredients Parts by Weight
______________________________________
Musk ambrette 40
Musk ketone 60
Coumarin 30
Oil of bergamot 150
Oil of lemon 100
Methyl ionone 50
Hexyl cinnamic aldehyde
100
Hydroxycitronellal 100
Oil of lavender 50
Texas cedarwood oil 85
Virginia cedarwood oil
30
Oil of sandalwood 40
(East Indies)
Isoeugenol 20
Eugenol 10
Benzyl acetate 30
.beta.-phenyl ethyl alcohoI
40
@-phenyl ethyl alcohol
30
Oakmoss absolute 30
Vetiver Oil Venezuela 25
The compound having the structure:
##STR19## 62
______________________________________
The compound having the structure:
##STR20##
imparts to this Chypre formulation green, vetivert, woody, earthy, orris,
minty, camphoraceous, cassis and grapefruit undertones with minty,
camphoraceous, green, herbaceous, vetivert and galbanum topnotes.
Accordingly, the formulation can be described from a perfumery standpoint
thusly:
"A Chypre aroma with green, vetivert, woody, earthy, orris, minty,
camphoraceous, cassis and grapefruit undertones and minty, camphoraceous,
green, herbaceous, vetivert and galbanum topnotes".
EXAMPLE III
Preparation of a Cosmetic Powder Composition
Cosmetic powder compositions are prepared by mixing in a ball mill, 100
grams of talcum powder with 0.25% grams of each of the substances set
forth in Table I below. Each of the cosmetic powder compositions has an
excellent aroma as described in Table I below:
TABLE I
______________________________________
Substance Aroma Description
______________________________________
##STR21## A green, vetivert, woody earthy, orris,
minty camphoraceous, cassis and grapefruit aroma with
minty, camphoraceous, green, vetivert and galbanum
topnotes.
Perfume composition of
A Chypre aroma with
Example II. green, vetivert, woody,
earthy, orris, minty,
camphoraceous, cassis and
grapefruit undertones and
minty, camphoraceous,
green, herbaceous,
vetivert and galbanum
topnotes.
______________________________________
EXAMPLE IV
Perfumed Liquid Detergents
Concentrated liquid detergents (Lysine salt of n-dodecylbenzene sulfonic
acid as more specifically described in U.S. Pat. No. 3,948,818 issued on
Apr. 6, 1976) with aroma nuances as set forth in Table I of Example III
are prepared containing 0.10%, 0.15%, 0.20%, 0.25%, 0.30% and 0.35% of the
substance set forth in Table I of Example III. They are prepared by adding
and homogeneously mixing the appropriate quantity of substance set forth
in Table I of Example III in the liquid detergent. The detergents all
possess excellent aroma as set forth in Table I of Example III, the
intensity increasing with greater concentrations of substance as set forth
in Table I of Example III.
EXAMPLE V
Preparation of Colognes and Handkerchief Perfumes
Compositions as set forth in Table I of Example III are incorporated into
colognes at concentrations of 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5% and 5.0%
in 80%,85%, 90% and 95% aqueous food grade ethanol solutions; and into
handkerchief perfumes at concentrations of 15%, 20%, 25% and 30% (in 80%,
85%, 90% and 95% aqueous food grade ethanol solutions). Distinctive and
definitive fragrances as set forth in Table I of Example III are imparted
to the colognes and to the and handkerchief perfumes at all levels
indicated.
EXAMPLE VI
Preparation of Soap Compositions
One hundred grams of soap chips [per sample]-IVORY.RTM., produced by the
Procter & Gamble Company of Cincinnati, Ohio), are each mixed with one
gram samples of substances as set forth in Table I of Example III until
homogeneous compositions are obtained. In each of the cases, the
homogeneous compositions are heated under 8 atmospheres pressure at
180.degree. C. for a period of three hours and the resulting liquids are
placed into soap molds. The resulting soap cakes, on cooling, manifest
aroma as set forth in Table I of Example III.
EXAMPLE VII
Preparation of Solid Detergent Compositions
Detergents are prepared using the following ingredients according to
Example III of Canadian Patent No. 1,007,948:
______________________________________
Ingredients Parts by Weight
______________________________________
"NEODOL .RTM. 45-11 12
(a C.sub.14 -C.sub.15 alcohol
ethoxylated with 11 moles of
ethylene oxide)
Sodium carbonate 55
Sodium citrate 20
Sodium sulfate, water brighteners
q.s.
______________________________________
This detergent is a phosphate-free detergent. Samples of 100 grams each of
this detergent are admixed with 0.10, 0.15, 0.20 and 0.25 grams of each of
the substances as set forth in Table I of Example III. Each of the
detergent samples has an excellent aroma as indicated in Table I of
Example III.
EXAMPLE VIII
Utilizing the procedure of Example III at column 15 of U.S. Pat. No.
3,632,396, non-woven cloth substrates useful as dry-added fabric softening
articles of manufacture are prepared wherein the substrate, the substrate
coating and the outer coating and the perfuming material are as follows:
1. A water "dissolvable" paper ("Dissolvo Paper");
2. Adogen 448 (m.p. about 140.degree. F.) as the substrate formulation
(m.p. about 150.degree. F.);
3. An outer coating having the following formulation (m.p. about
150.degree. F.):
57%--C.sub.20-22 HAPS
22%--isopropyl alcohol
20%--antistatic agent
1%--of one of the substances as set forth in Table I of Example III.
Fabric softening compositions prepared according to Example III at column
15 of U.S. Pat. No. 3,632,396 having aroma characteristics as set forth in
Table I of Example III, consist of a substrate coating consisting of about
1.85 grams per 100 square inches of substrate; and an outer coating coated
on the first coating consisting of about 1.4 grams per 100 square inches
of substrate. One of the substances of Table I of Example III is admixed
in each case with the outer coating mixture, thereby providing a total
aromatized outer coating weight ratio to substrate of about 0.5:1 by
weight of the substrate. The aroma characteristics are imparted in a
pleasant manner to the head space in a dryer on operation thereof in each
case using said dryer-added fabric softener non-woven fabrics and these
aroma characteristics are described in Table I of Example III.
EXAMPLE IX
Hair Spray Formulations
The following hair spray formulation is prepared by first dissolving PVP/VA
E-735 copolymer manufactured by the GAF Corporation of 140 West 51st
Street, New York, New York, in 91.62 grams of 95% food grade ethanol, 8.0
grams of the polymer is dissolved in the alcohol. The following
ingredients are added to the PVP/VA alcoholic solution:
______________________________________
Ingredients Parts by Weight
______________________________________
Dioctyl sebacate 0.05
Benzyl alcohol 0.10
Dow Corning 473 fluid 0.10
(prepared by the Dow Corning Corporation)
Tween 20 surfactant 0.03
(prepared by ICI America Corporation
One of the perfumery substances as set
0.10
forth in Table I of Example III.
______________________________________
The perfuming substances as set forth in Table I of Example III add aroma
characteristics as set forth in Table I of Example III which are rather
intense and aesthetically pleasing to the users of the soft-feel,
good-hold pump hair sprays.
EXAMPLE X
Conditioning Shampoos
Monamid CMA (prepared with the Mona Industries Company) (3.0 weight
percent) is melted with 2.0 weight percent coconut fatty acid (prepared by
Procter & Gamble Company of Cincinnati, Ohio); 1.0 weight percent ethylene
glycol disterate (prepared by the Armak Corporation) and triethanolamine
(a product of Union Carbide Corporation) (1.4 weight percent). The
resulting melt is admixed with Stepanol WAT produced by the Stepan
Chemical Company (35.0 weight percent). The resulting mixture is heated to
60.degree. C. and mixed until a clear solution is obtained (at 60.degree.
C.).
GAFQUA.RTM. 755N polymer (manufactured by GAF Corporation of 140 West 51st
Street, New York, New York) (5.0 weight percent) is admixed with 0.1
weight percent sodium sulfite and 1.4 weight percent polyethylene glycol
6000 distearate produced by Armak Corporation.
The resulting material is then mixed and cooled to 45.degree. C. and 0.3
weight percent of perfuming substance as set forth in Table I of Example
III is added to the mixture. The resulting mixture is cooled to 40.degree.
C. and blending is carried out for an additional one hour in each case. At
the end of this blending period, the resulting material has a pleasant
fragrance as indicated in Table I of Example III.
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